US4985585A - Phenoxyalkylcarboxylic acid derivatives and process for their preparations - Google Patents

Phenoxyalkylcarboxylic acid derivatives and process for their preparations Download PDF

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Publication number
US4985585A
US4985585A US07/313,900 US31390089A US4985585A US 4985585 A US4985585 A US 4985585A US 31390089 A US31390089 A US 31390089A US 4985585 A US4985585 A US 4985585A
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US
United States
Prior art keywords
group
acetyl
ethyl
oil
compounds
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
US07/313,900
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English (en)
Inventor
Mitsuo Ohashi
Katsuya Awano
Toshio Tanaka
Tetsuya Kimura
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Kyorin Pharmaceutical Co Ltd
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Kyorin Pharmaceutical Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Kyorin Pharmaceutical Co Ltd filed Critical Kyorin Pharmaceutical Co Ltd
Assigned to KYORIN PHARMACEUTICAL CO., LTD. reassignment KYORIN PHARMACEUTICAL CO., LTD. ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: AWANO, KATSUYA, KIMURA, TETSUYA, OHASHI, MITSUO, TANAKA, TOSHIO
Application granted granted Critical
Publication of US4985585A publication Critical patent/US4985585A/en
Priority to US10/622,589 priority Critical patent/USRE38921E1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/24—Sulfones; Sulfoxides having sulfone or sulfoxide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides

Definitions

  • this reaction is conducted in an organic solvent, for example acetone, methylethylketone, diethylketone or dimethylformamide etc. under a reaction temperature of the room temperature to the solvent refluxing temperature.
  • an organic solvent for example acetone, methylethylketone, diethylketone or dimethylformamide etc.
  • an inorganic base for example potassium carbonate or sodium carbonate etc. and further the addition of potassium iodide are also recommendable.
  • Example 31 the title compound was obtained as pale yellow oil with yield of 81.0%.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
US07/313,900 1988-03-07 1989-02-23 Phenoxyalkylcarboxylic acid derivatives and process for their preparations Ceased US4985585A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US10/622,589 USRE38921E1 (en) 1988-03-07 2003-07-21 Phenoxyalkylcarboxylic acid derivatives and process for their preparations

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP63-53374 1988-03-07
JP5337488 1988-03-07

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US10/622,589 Reissue USRE38921E1 (en) 1988-03-07 2003-07-21 Phenoxyalkylcarboxylic acid derivatives and process for their preparations

Publications (1)

Publication Number Publication Date
US4985585A true US4985585A (en) 1991-01-15

Family

ID=12941043

Family Applications (2)

Application Number Title Priority Date Filing Date
US07/313,900 Ceased US4985585A (en) 1988-03-07 1989-02-23 Phenoxyalkylcarboxylic acid derivatives and process for their preparations
US10/622,589 Expired - Lifetime USRE38921E1 (en) 1988-03-07 2003-07-21 Phenoxyalkylcarboxylic acid derivatives and process for their preparations

Family Applications After (1)

Application Number Title Priority Date Filing Date
US10/622,589 Expired - Lifetime USRE38921E1 (en) 1988-03-07 2003-07-21 Phenoxyalkylcarboxylic acid derivatives and process for their preparations

Country Status (9)

Country Link
US (2) US4985585A (fr)
EP (1) EP0332109B1 (fr)
KR (1) KR960007602B1 (fr)
CN (1) CN1022407C (fr)
AU (1) AU617439B2 (fr)
CA (1) CA1331763C (fr)
DE (1) DE68900485D1 (fr)
ES (1) ES2045219T3 (fr)
HU (2) HU208524B (fr)

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU638626B2 (en) * 1991-01-18 1993-07-01 Kyorin Pharmaceutical Co. Ltd. Phenoxyalkylcarboxylic acid derivatives and process of preparing the same
US20040267041A1 (en) * 2003-06-24 2004-12-30 Locke Kenneth Walter Process for making polymorphic form A of 4-[6-acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenylthio)propoxy]-2-propylphenoxy]butyric acid
US20040266878A1 (en) * 2003-06-24 2004-12-30 Locke Kenneth Walter Polymorphic form A of 4-[6-acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenylthio)propoxy]-2-propylphenoxy]butyric acid
USRE38921E1 (en) 1988-03-07 2005-12-13 Kyorin Pharmaceutical Co., Ltd. Phenoxyalkylcarboxylic acid derivatives and process for their preparations
US7429617B2 (en) 2004-04-27 2008-09-30 Medicinova, Inc. Phenoxyalkycarboxylic acid derivatives in the treatment of interstitial cystitis
EP1997491A1 (fr) 2004-07-14 2008-12-03 Inflammation Research Center Company Ltd. Procédé d'inhibition d'une métastase de tumeur
US8835499B2 (en) 2011-12-08 2014-09-16 Medicinova, Inc. Method of treating non-alcoholic fatty liver disease and steatohepatitis
WO2015013395A1 (fr) 2013-07-25 2015-01-29 Medicinova, Inc. Procédés pour réduire les niveaux de sang de triglycéride, de cholestérol total et de lipoprotéine de basse densité
US8962687B2 (en) 2012-12-05 2015-02-24 Medicinova, Inc. Method of treating liver disorders
WO2015171755A2 (fr) 2014-05-08 2015-11-12 Medicinova, Inc. Procédé de traitement d'une stéatohépatite non alcoolique avancée
WO2015187548A1 (fr) 2014-06-02 2015-12-10 Medicinova, Inc. Procédé d'inhibition ou de traitement de la fibrose
EP3763362A1 (fr) 2014-05-08 2021-01-13 MediciNova, Inc. Procédé de traitement d'une fibrose pulmonaire idiopathique
WO2022251464A1 (fr) 2021-05-28 2022-12-01 Medicinova, Inc. Dérivés d'acide phénoxyalkylcarboxylique et leur utilisation pour abaisser les taux de triglycérides

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100784653B1 (ko) 2000-01-26 2007-12-12 교린 세이야꾸 가부시키 가이샤 점안제

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2058785A (en) * 1979-09-05 1981-04-15 Glaxo Group Ltd Phenol Derivatives
EP0056172A2 (fr) * 1981-01-09 1982-07-21 FISONS plc Composés contenant les restes phénoxy et/ou thiophénoxy, méthodes pour la préparation de ces composés et compositions pharmaceutiques les contenant
US4507498A (en) * 1982-04-09 1985-03-26 Hoffmann-La Roche Inc. Phenoxycarboxylic acids

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL69691A (en) * 1982-09-23 1988-01-31 Merck Frosst Canada Inc Leukotriene antagonists,their preparation and pharmaceutical compositions containing them
AU7450087A (en) * 1987-05-22 1988-11-24 Lunam, M.A. Pillow
JPH0819041B2 (ja) 1987-09-10 1996-02-28 杏林製薬株式会社 フェノキシアルキルカルボン酸誘導体及びその製造法
US4985585A (en) 1988-03-07 1991-01-15 Kyorin Pharmaceutical Co., Ltd. Phenoxyalkylcarboxylic acid derivatives and process for their preparations
US5290812A (en) 1991-01-18 1994-03-01 Kyorin Pharmaceutical Co., Ltd. Phenoxyalkylcarboxylic acid derivatives and process of preparing the same

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2058785A (en) * 1979-09-05 1981-04-15 Glaxo Group Ltd Phenol Derivatives
EP0056172A2 (fr) * 1981-01-09 1982-07-21 FISONS plc Composés contenant les restes phénoxy et/ou thiophénoxy, méthodes pour la préparation de ces composés et compositions pharmaceutiques les contenant
US4507498A (en) * 1982-04-09 1985-03-26 Hoffmann-La Roche Inc. Phenoxycarboxylic acids

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
Burger, "Medicinal Chemistry," 2nd Ed. pp. 72-88 (1960).
Burger, Medicinal Chemistry, 2nd Ed. pp. 72 88 (1960). *

Cited By (36)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
USRE38921E1 (en) 1988-03-07 2005-12-13 Kyorin Pharmaceutical Co., Ltd. Phenoxyalkylcarboxylic acid derivatives and process for their preparations
AU638626B2 (en) * 1991-01-18 1993-07-01 Kyorin Pharmaceutical Co. Ltd. Phenoxyalkylcarboxylic acid derivatives and process of preparing the same
US7728169B2 (en) 2003-06-24 2010-06-01 Medicinova, Inc. Pharmaceutical compositions of isolated orthorhombic crystalline 4-[6-acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenylthio)propoxy]-2-propylphenoxy]butyric acid and methods of use
WO2005000243A3 (fr) * 2003-06-24 2005-04-28 Medicinova Inc Forme polymorphe de l'acide 4-[6-acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenylthio)propoxy]-2-propylphenoxy]butyrique
US20040266878A1 (en) * 2003-06-24 2004-12-30 Locke Kenneth Walter Polymorphic form A of 4-[6-acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenylthio)propoxy]-2-propylphenoxy]butyric acid
US20060106105A1 (en) * 2003-06-24 2006-05-18 Medicinova, Inc. Process for making polymorphic form a of 4-[6-acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenylthio)propoxy]-2-propylphenoxy] butyric acid
US7060854B2 (en) 2003-06-24 2006-06-13 Medicinova, Inc. Process for making polymorphic form A of 4-[6-acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenylthio)propoxy]-2-propylphenoxy]butyric acid
US7064146B2 (en) * 2003-06-24 2006-06-20 Medicinova, Inc. Pharmaceutical compositions of isolated orthorhombic crystalline 4-[6-acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenylthio)propoxy]-2-propylphenoxy]butyric acid and methods of use
US20060135604A1 (en) * 2003-06-24 2006-06-22 Medicinova, Inc. Pharmaceutical compositions of isolated orthorhombic crystalline 4-[6-acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenylthio)propoxy]-2-propylphenoxy]butyric acid and methods of use
US7153993B2 (en) 2003-06-24 2006-12-26 Medicinova, Inc. Process for making polymorphic form A of 4-[6-acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenylthio)propoxy]-2-propylphenoxy]butyric acid
WO2005000242A3 (fr) * 2003-06-24 2007-08-23 Medicinova Inc Procede d'obtention de l'acide 4-[6-acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenylthio)propoxy]butyrique, polymorphe de forme a
RU2317979C2 (ru) * 2003-06-24 2008-02-27 Медсинова, Инк. Изолированная орторомбическая кристаллическая форма 4-[6-ацетил-3-[3-(4-ацетил-3-гидрокси-2-пропилфенилтио)пропокси]-2-пропил-фенокси]масляной кислоты и фармацевтическая композиция на ее основе
CN1812968B (zh) * 2003-06-24 2016-07-27 美迪诺亚公司 4-[6-乙酰基-3-[3-(4-乙酰基-3-羟基-2-丙基苯硫基)丙基]-2-丙基苯氧基]丁酸的多晶型物
US7365224B2 (en) 2003-06-24 2008-04-29 Medicinova, Inc. Pharmaceutical compositions of isolated orthorhombic crystalline 4-[6-acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenylthio)propoxy]-2-propylphenoxy]butyric acid and methods of use
US20080292698A1 (en) * 2003-06-24 2008-11-27 Medicinova, Inc. Pharmaceutical compositions of isolated orthorhombic crystalline 4-[6-acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenylthio)propoxy]-2-propylphenoxy]butyric acid and methods of use
US20040267041A1 (en) * 2003-06-24 2004-12-30 Locke Kenneth Walter Process for making polymorphic form A of 4-[6-acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenylthio)propoxy]-2-propylphenoxy]butyric acid
US7786169B2 (en) 2004-04-27 2010-08-31 Medicinova, Inc. Phenoxyalkycarboxylic acid derivatives in the treatment of ulcerative colitis
RU2388466C2 (ru) * 2004-04-27 2010-05-10 Медисинова, Инк. Производные феноксиалкилкарбоновых кислот при лечении воспалительных заболеваний
US20090093545A1 (en) * 2004-04-27 2009-04-09 Medicinova, Inc. Phenoxyalkycarboxylic acid derivatives in the treatment of irritable bowel syndrome or ulcerative colitis
US7429617B2 (en) 2004-04-27 2008-09-30 Medicinova, Inc. Phenoxyalkycarboxylic acid derivatives in the treatment of interstitial cystitis
US8026282B2 (en) 2004-04-27 2011-09-27 Medicinova, Inc. Phenoxyalkylcarboxylic acid derivatives in the treatment of irritable bowel syndrome
US20100285074A1 (en) * 2004-04-27 2010-11-11 Medicinova, Inc. Phenoxyalkylcarboxylic acid derivatives in the treatment of irritable bowel syndrome
EP1997491A1 (fr) 2004-07-14 2008-12-03 Inflammation Research Center Company Ltd. Procédé d'inhibition d'une métastase de tumeur
US9012509B2 (en) 2011-12-08 2015-04-21 Medicnova, Inc. Method of treating non-alcoholic steatohepatitis
US8835499B2 (en) 2011-12-08 2014-09-16 Medicinova, Inc. Method of treating non-alcoholic fatty liver disease and steatohepatitis
US8962687B2 (en) 2012-12-05 2015-02-24 Medicinova, Inc. Method of treating liver disorders
WO2015013395A1 (fr) 2013-07-25 2015-01-29 Medicinova, Inc. Procédés pour réduire les niveaux de sang de triglycéride, de cholestérol total et de lipoprotéine de basse densité
US9358217B2 (en) 2013-07-25 2016-06-07 Medicinova, Inc. Methods for reducing triglyceride, total cholesterol and low density lipoprotein blood levels
WO2015105874A1 (fr) 2014-01-10 2015-07-16 Medicinova, Inc. Méthode de traitement de troubles hépatiques
EP3091972A4 (fr) * 2014-01-10 2017-08-23 MediciNova, Inc. Méthode de traitement de troubles hépatiques
WO2015171755A2 (fr) 2014-05-08 2015-11-12 Medicinova, Inc. Procédé de traitement d'une stéatohépatite non alcoolique avancée
EP3763362A1 (fr) 2014-05-08 2021-01-13 MediciNova, Inc. Procédé de traitement d'une fibrose pulmonaire idiopathique
WO2015187548A1 (fr) 2014-06-02 2015-12-10 Medicinova, Inc. Procédé d'inhibition ou de traitement de la fibrose
US9498458B2 (en) 2014-06-02 2016-11-22 Medicinova, Inc. Method of inhibiting or treating fibrosis
WO2022251464A1 (fr) 2021-05-28 2022-12-01 Medicinova, Inc. Dérivés d'acide phénoxyalkylcarboxylique et leur utilisation pour abaisser les taux de triglycérides
US12239620B2 (en) 2021-05-28 2025-03-04 Medicinova, Inc. Methods to decrease triglyceride synthesis in the liver

Also Published As

Publication number Publication date
KR960007602B1 (ko) 1996-06-07
HU912411D0 (en) 1991-12-30
AU3088489A (en) 1989-09-07
CN1036560A (zh) 1989-10-25
ES2045219T3 (es) 1994-01-16
EP0332109A1 (fr) 1989-09-13
HU208524B (en) 1993-11-29
KR890014435A (ko) 1989-10-23
CN1022407C (zh) 1993-10-13
DE68900485D1 (de) 1992-01-16
HU204030B (en) 1991-11-28
EP0332109B1 (fr) 1991-12-04
HUT50112A (en) 1989-12-28
CA1331763C (fr) 1994-08-30
AU617439B2 (en) 1991-11-28
USRE38921E1 (en) 2005-12-13

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